


Dean Winchester's Guide to Festive Masturbation

by doilycoffin



Series: Wincest Love Week (Fall 2016) [2]
Category: Supernatural
Genre: Blow Jobs, Food Sex, I've lost control of my life, M/M, Weird smut
Language: English
Status: Completed
Published: 2016-11-28
Updated: 2016-11-30
Packaged: 2018-09-02 22:26:32
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,435
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8685679
Author URL: https://archiveofourown.org/users/doilycoffin/pseuds/doilycoffin
Summary: When Sam leaves Dean all alone at the bunker for nearly a week, he's nearly positive that he'll perish from lack of sex. So, really, it's not his fault that he had to turn to the produce section of a grocery store to fulfill his needs. Too bad Sam had to come home early though.





	1. Chapter 1

**Author's Note:**

> Written for the prompt "pumpkin fuckin'"

 

To be completely fair, the whole thing was at least partially Sam’s fault. If he hadn’t been gone for most of the week on a nerdy-ass Research Jamboree with two other hunters, cruelly leaving Dean behind at the bunker alone to suffer a slow, lingering death by way of blue balls, then Dean wouldn’t have been driven to such lengths in the first place. Sam could have very easily declined when Max called him and sweet talked him into helping him and his sister with conducting research for a particularly confounding hunt in the next state over, but Sam just couldn’t resist when Max mentioned that they had some rare, ridiculously old texts that he’d be happy to let Sam take a gander at in return for his assistance.

Needless to say, Dean wasn’t exactly thrilled that his brother was spending some quality time with a guy who clearly had boner for him and was quite possibly planning to seduce and/or bewitch him the moment the moment they were alone together. In hindsight, it was probably a bad idea to actually verbalize those thoughts to Sam, who didn’t take kindly to Dean disparaging his new buddy, and he responded predictably poorly to Dean’s subsequent, extremely rational interrogation that included such questions as “can’t you just do research with them on skype or something?” and “have you considered that maybe the monster is just some dude wearing a rubber mask who’s watched too much Scooby Doo?,” and, most importantly, “how the hell did Sabrina the teenage witch get your phone number anyway?”

Alas, his expert logistical skills were, sadly, unable to sway Sam from going on the trip. While Dean probably could have at least wheedled and pouted his way into going along with him, his pride stopped him and he instead told Sam that, yes, he totally trusted Max despite the fact that he was a witch (he didn’t); no, he wasn’t the slightest bit jealous at the idea of Sam spending time alone with Max (he was); of course he could spend a whole week away from Sam because it’s not like his whole world revolved around the guy or anything like that (it did); and he could totally last a whole week devoid of incestuous nookie (well, theoretically speaking, he probably could, but what kind of quality of life was that?)

As he reflected upon all of this, he came to the sound conclusion that it was almost certainly mostly Sam’s fault (at least 70% if he was being conservative) that Dean was currently sitting at the kitchen table and contemplating sticking his dick into a pumpkin.

Well, okay, he had already carved a hole in it that was large enough to fit his dick through (which made it an extremely respectably sized hole in his opinion), so he was a little bit beyond the stage of merely mulling the whole idea over and more into the stage of imminently fucking a pumpkin.

It’s not that he’d always secretly lusted after big, orange gourds or anything, but he had to admit that he’d been curious about the whole thing after coming across a surprisingly large array of porn dedicated to it. For a long time it had been an idle curiosity rather than something he ever genuinely thought he’d do, but when he went on a grocery run earlier in the day, he found himself lingering in the produce section and thought “why the hell not?”. Sam was out of town anyway so it’s not like he could walk in on him doing it, and Dean was miserably horny (due to the aforementioned problem of Sam being out of town), which created ideal conditions for pumpkin fucking if he had ever heard of them, especially since he managed to find the perfect pumpkin to do it with.

Feeling resolved, Dean stared at his handiwork with a weird sense of pride. Damn, he knew how to pick a bangable pumpkin. He briefly considered drawing a face on it or something to give it more character, but quickly decided against it; he was about to put his dick in a pumpkin, sure, but he wasn’t going to be _weird_ about it.

Without further ado, Dean unbuckled his belt, pushed down his jeans and underwear in one motion, and positioned himself behind the pumpkin that was still perched on the table, sliding slowly into it until his balls rested against against the shell. For a second, he didn’t move at all and cataloged the sensation of it. The inside of the pumpkin was warmer than he thought it would be (inviting in a way) and it was kind of like fucking the world’s goopiest flesh-light. All in all, it definitely wasn’t the worst thing his dick had been inside of (and it had been in some interesting places, he had to admit) and he slowly began thrusting in and out, making a squelching noise so loud and dirty that a blush found its way onto his cheeks even though there was no one there to hear it. After a few self-conscious thrusts, he realized that he was actually starting to get really into the whole thing and began pumping his hips more furiously as moans tore themselves from his parted lips.

After a few more minutes, he was so close to the edge of release that he didn’t even realize that someone had opened the front door of the bunker until Sam stood right in front of him, gaping at the sight of Dean fucking a pumpkin while his pants were around his ankles.

They both stared at each other speechlessly until Dean figured that the burden of breaking the silence was probably on his shoulders.

“This, uh. This is pretty much exactly what you think it is,” he admitted as he watched Sam’s mouth open and close several times without speaking any actual words.

“Yeah, it was kind of hard to misinterpret this in any way,” Sam said once the shock of the situation wore off. “I just…why?”

Dean shrugged unapologetically, hoping that he could deter Sam from making fun of him for a million years if he acted nonchalant and generally like it was completely normal for him to be walked in on while fucking produce.

“C’mon Sammy, don’t tell me you’ve never thought about doing this.”

“I really, really haven’t,” Sam pointed out. “Like, ever.”

“Seriously? I can give you a turn if you want,” he offered generously, snickering at the way Sam’s face turned red.

“I’m not taking a turn with your fuck-pumpkin!”Sam sputtered indignantly.

“I’ve actually been calling it a jackoff lantern but–”

Sam held up a hand to signal Dean to shut up.

“I’m sorry, but I really can’t take you seriously when your dick is literally still inside of the pumpkin.”

Dean rolled his eyes and slowly extracted himself, noting that his dick was still covered with the innards of the pumpkin.

“Happy now, princess?” he asked sarcastically. “You know, I thought you would be flattered by the whole thing.”

Sam’s brow furrowed as he tried to figure out on what planet he would be flattered by the idea of someone screwing a pumpkin.

“What the hell are you talking about?”

Dean sighed in frustration as he gestured at the pumpkin.

“I mean that the pumpkin is almost a perfect replica of your ass,” he explained as if it were the most obvious thing in the world.

Sam frowned and leaned forward to study the pumpkin more closely and reluctantly admitted to himself that the crease in the middle of it separating the two rounded halves actually did make it look vaguely ass-like.

“…you bought and proceeded to fuck a pumpkin because you think it looks like my ass? How messed up is it that I actually think that’s sweet?”

“If you really think so, then how about you show me your appreciation?,” Dean asked suggestively as he leered at his brother.

Sam scoffed. “Yeah, right. Maybe after you shower,” he said as he stared pointedly at Dean’s pumpkin covered dick.

“I think I know some better ways that you can clean it,” Dean implored. “Come on, Sam, you might like it. Hell, a pumpkin-y blowjob is just plain festive when you think about it. Get into the holiday spirit.”

Sam gave his brother an exasperated look, but sank to his knees readily enough and stuck his tongue out to lick an experimental stripe up the length of Dean’s dick, tasting the essence of pumpkin that lingered on it.

“It’s kind of tangy,” he concluded thoughtfully. “But still a little sweet.”

“That’s a brilliant scientific observation, but maybe you can save it until after you–”

Before Dean could finish his quip and quite possibly talk himself out of a blowjob, Sam swallowed him down with practiced ease and Dean was fortunately too busy fucking his brother’s face to properly deliver snark.

Sam ended up picking pumpkin strands out of his teeth for hours afterward, but Dean was pretty sure that his Great Pumpkin Fucking Adventure had been a rousing success.


	2. Chapter 2

**Notes for the Chapter:**

> I previously had no intention of continuing this fic, but 3White_Mage3 proposed the idea of Dean being outraged at the fact that Sam's dick is too big to fit in the pumpkin hole and the idea tickled me so much that I had to write it. Enjoy!

“I don’t...think it’s gonna to fit,” Sam admitted as he futilely tried to nudge his dick through the slightly undersized pumpkin-gloryhole. Prior to today, he had never foreseen such a thing as being a dilemma he would have to grapple with because he had been living his life under the general assumption that he would never feel the urge to fuck a pumpkin in the first place. But then again, being around Dean Winchester on a constant basis tended to make you do weird shit, so he probably should have prepared for it anyway. 

For several hours after the Pumpkin Incident, Dean had incessantly prodded Sam to give the whole “pumpkin fucking” thing a try, first by attempting to convince him of how good it would feel and then, when that failed to persuade him, he had moved on to teasing Sam and calling him too “tragically vanilla to stick [his] dick in a perfectly good jackoff lantern.” 

Frankly, Sam was almost 100% sure that the only _real_ reason Dean wanted him to bang a pumpkin was because he believed that Sam couldn’t make fun of _him_ for doing it if he were a part of the same weird Gourd Fetishism club. In the end though, he agreed to do it anyway under the condition that Dean never again say the words “jackoff lantern,” which was a promise that was (very reluctantly) agreed upon. 

At any rate, that was why Sam was currently standing in front of a pumpkin, sans pants, and trying to stuff his dick inside of it as his voyeuristic brother looked on from the kitchen table. 

“What do you mean it won’t fit? Is the hole too big for you or something?,” Dean asked gleefully. 

Sam pinned his brother with a glare. “Try the opposite of that,” he answered dryly (and, yes, a little smugly. Sue him.) 

“Well, it can’t possibly be too small! Mine fit through it just fine.”

“Do you really need me to spell this out for you?”

“And if your dick is too big to fit though the hole,” Dean continued, ignoring Sam, “then that obviously means that _my_ dick isn’t too big for it since I used said hole earlier, which would then imply that your dick is bigger than mine, _which isn’t fucking possible_.”

“Wow. You really took a winding road on that one but, yeah, that’s what I’m saying.” 

His brother looked about as offended as Sam had ever seen him. Even more so than that one time that he had tried to trick Dean into eating a low-calorie sugar-free cherry pie, and he got the silent treatment for _days_ after that stunt. 

“T-that’s insane. I can’t believe what I’m hearing,” Dean sputtered in shock as he put his head in his hands. 

It was a bit overly dramatic in Sam’s opinion. “You can’t possibly _still_ be in denial about this,” he argued. “You see my junk like all the time. You’re so familiar with it that you could probably pick it out in a line-up, so you definitely know how big it is.” 

“I think I would have noticed if it were bigger than mine! Maybe yours just _seems_ bigger right now for some reason. Maybe you...had an allergic reaction to something and it’s swollen.”

Sam narrowed his eyes. “An allergic reaction concentrated solely on my dick?” 

“Just because you don’t watch _Dr. Sexy_ doesn’t mean the rest of us don’t,” Dean griped. “There was totally an episode where that happened once.” 

In the face of his brother’s delusions, Sam sighed heavily and began to regret many of his life choices. “Look, I’m not saying that it’s _much_ bigger. Just slightly,” he placated. “And just because it’s larger doesn’t mean yours is small. It’s still pretty freakin’ huge, and I’ve been fucked by it enough times to say that and mean it.”

“It _is_ pretty impressive...,” Dean conceded, a little less glumly now. 

“Exactly. And if you wanna get real technical, mine is probably only bigger because I’m so much taller and my dick is proportional to that. If we take that into account then your dick is, proportionally speaking, possibly bigger than mine. Maybe. Ish.” 

Dean face lit up with hope. “You really think so?”

“Sure,” Sam with relief at the fact that they could finally get over the Great Dick Debate, “why not?”

Eager to take Dean’s mind off of the whole thing, Sam turned his attention once again to the now-forgotten pumpkin that was languishing sadly on the table and began turning it around in his hands appraisingly.

“You know...” he said thoughtfully, “I could probably carve a bigger hole in this thing on the opposite end. Then we could both fuck it at the same time.” 

“Now that’s what I’m talkin’ about,” Dean whooped as he rubbed his hands together in anticipation. “For a guy who’s so reluctant to fuck a pumpkin, you’re a real innovator when it comes to this sort of thing.”

“Yeah, yeah, just take off your damn pants...” 

“Hey, if you wanna get _really_ kinky, we could probably try making it into a pie after we get finished. A ‘ _cum_ pkin’ pie if you will.”

Sam’s face drew into a disgusted expression. “Dude!” 

“What? Too much?”

“ _Way_ too much. I still have my limits.” 

Dean gave him a winning smirk as he shoved his pants down and prepared to engage in his pumpkin ménage à trois. “We’ll just have to see about that, Sammy.”


End file.
